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Beta-cyclocostunolide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C=C1CCC[C@]2([C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CC2)C |
|---|---|
| InChI | InChI=1S/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15+/m0/s1 |
| InChIKey | XUYAKPXYKQEFPD-SFDCQRBFSA-N |
| Formula | C15H20O2 |
| HBA | 2 |
| HBD | 0 |
| MW | 232.32 |
| Rotatable Bonds | 0 |
| TPSA | 26.3 |
| LogP | 3.24 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 232.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea acaulis | Asteraceae | Plantae | 2969722 |
Showing of synonyms
Beta-cyclocostunolide
2221-82-1
CID 442192
(3aS,5aR,9aS,9bS)-5a-methyl-3,9-dimethylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
C09384
CHEMBL4759939
SCHEMBL15941718
CHEBI:10364
DTXSID60331766
Naphtho[1,2-b]furan-2(3H)-one, decahydro-5a-methyl-3,9-dimethylene-, (3aS,5aR,9aS,9bS)-
Q27108625
- Bentamène A, Benayache S, et al. (2005). A new guaianolide and other sesquiterpene lactones from Centaurea acaulis L. (Asteraceae). Biochemical Systematics and Ecology,2005,33,1061-1065. [View]
Pubchem:
442192
Cas:
2221-82-1
Kegg Ligand:
C09384
Chebi:
10364
Nmrshiftdb2:
60024332
Chembl:
CHEMBL4759939
Comptox:
DTXSID60331766
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)C3C(CC2)CCCC3=C
Level: 0
Mol. Weight: 232.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.72
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.39
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.38
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.77
- Plasma Protein Binding
- 52.0
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.04
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.8
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.43
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.96
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 1.97
- Rat (Acute)
- 2.2
- Rat (Chronic Oral)
- 1.6
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 311.25
- Hydration Free Energy
- -3.2
- Log(D) at pH=7.4
- 3.09
- Log(P)
- 3.19
- Log S
- -3.95
- Log(Vapor Pressure)
- -3.48
- Melting Point
- 84.98
- pKa Acid
- 10.1
- pKa Basic
- 7.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7778 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7778 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7776 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7776 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7700 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7700 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7449 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7449 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7417 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7417 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7223 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7223 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7172 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7172 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7143 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7143 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7024 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7024 |